Potassium Carbonate → Benzyl(S)-2-((2'-cyanobiphenyl-4-ylmethyl)pentanoylamino)-3-methylbutyrate

HRID 550036Notes

Reaction equation

HRID 550036 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:8]([O:15][C:16](=[O:37])[C@H:17]([CH:34]([CH3:36])[CH3:35])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]#[N:33])=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:38](Cl)(=[O:43])[CH2:39][CH2:40][CH2:41][CH3:42]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.ClCCl>[CH2:8]([O:15][C:16](=[O:37])[C@H:17]([CH:34]([CH3:35])[CH3:36])[N:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]#[N:33])=[CH:24][CH:25]=1)[C:38](=[O:43])[CH2:39][CH2:40][CH2:41][CH3:42])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 61186Valeryl chlorideHCID 44252740HCID 44252740, compound

Product 1

HCID 46912012Benzyl(S)-2-((2'-cyanobiphenyl-4-ylmethyl)pentanoylamino)-3-methylbutyrate

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of potassium carbonate (95.3 g) and de-mineralized water (100 ml) was stirred for 10 to 15 minutes to dissolve the solid. The temperature of the mixture was maintained at 25° to 30° C. and dichloromethane (300 ml) was added to the mixture. (S)—N-[(2′-Cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester hydrochloride (100 g) and tetrabutyl ammonium bromide (10.0 g) were added to the mixture. The reaction mixture was cooled to −10° to −8° C. and valeryl chloride (36.1 g) was added at −10° to −5° C. The reaction mixture was stirred for 60 to 90 minutes at 0° to 5° C. After the completion of the reaction, the temperature was raised to 25° to 30° C. De-mineralized water (200 ml) was added to the reaction mixture and the mixture was stirred for 1 hour at 25° to 30° C. The two phases were separated and the organic layer was washed with de-mineralized water (200 ml). The organic layer was concentrated at 40° to 45° C. to obtain a residual liquid containing the title compound.

Workup

  1. dissolutionto dissolve the solid
  2. temperatureThe temperature of the mixture was maintained at 25° to 30° C.
  3. temperatureThe reaction mixture was cooled to −10° to −8° C.
  4. stirringThe reaction mixture was stirred for 60 to 90 minutes at 0° to 5° C
  5. customAfter the completion of the reaction
  6. temperaturethe temperature was raised to 25° to 30° C
  7. stirringthe mixture was stirred for 1 hour at 25° to 30° C
  8. customThe two phases were separated
  9. washthe organic layer was washed with de-mineralized water (200 ml)
  10. concentrationThe organic layer was concentrated at 40° to 45° C.
  11. customto obtain a residual liquid

Sources & evidence

ORD record
ord-16ff3ddfe4f745d4851d7da5322ae0a0
Source dataset
uspto-grants-2011_05
Patent number
US07943794B2

Reaction notes

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